Tough Luck
by fanficfanatic5000
Summary: Ash Ketchum is going to middle school. But can he handle the drama of it all, or will he crack under the pressure of his big dream, being a pokemon master, and picking the right friends to do so? Will he even win his battles in school? Will he get a girlfriend? Ash will find out in this story.
1. Prologue: Ash and Misty

**Prologue**:

Ash Ketchum, from Pallet, was going to his first day of middle school. There, he would learn the six main subjects, which where Math, Reading, Writing, History, Pokemon Training, and Battle Srategy Class. He was walking to the school with his best friend from elementary school, Misty Waterflower. Despite their continuous arguments, Ash and Misty were still together, and had a friendship as close as one could be.

"Hey Ash," said Misty. "What do you think our first day of middle school will be like?"

"I`m not sure Misty." Ash replied. "I hope it'll be really fun!"

"Yeah your right. Think any of our old friends will be there?"

"Of course Misty!"

"Pika, Pikachu!"

"Excuse me," a man they didn't know said to them as they walked through the playground beside the school. " "While your on school grounds, all pokemon must remain in their pokeballs."

"May I ask who you are?" Replied Misty.

"I am the principal here, and what are you twos names? I don't recognize you."

"I'm Ash and this is Misty, nice to meet you sir"

"Okay, great. I'm sorry but I will have to ask you again, please all pokemon in their pokeballs, please."

"Yes sir, sorry Pikachu"

"Pika, Pika"

**Now it's time for Ash and Misty to begin their first day of school. But what surprises await them? Will this new school prove to be a challenge? We will have to find out, in the first chapter of course!**


	2. Chapter 1: Class with GARY?

**Chapter 1:**

"I_ didn't expect to see YOU here" _ said Ash.

"I think this school will be lovely!" Said Serena

"Great! So Serena, and Misty, wanna go check out the class lists?" Asked Ash

"Okay," Misty replied.

"Sweet!" Serena squealed. "Us three have every class together!"

"Along with May, Drew, Paul, Dawn, Trip, Iris, and Gary" Misty listed off.

"Not Gary!" Ash said.

"Look on the bright side, Ash, almost all of our elementary friends are in our classes" Misty replied.

Misty and Ash than began to argue about who would get the better final grade in the pokemon training class, and who would do this and that before the other, and the argument ended with laughter from all three of the friends. No matter how much they wanted to be better than each other, they still were great friends.

And soon after, the bell rang, and the three had to hurry to class or they'd end up late. Misty and Ash picked seats next to each other, while Serena sat more towards the front of the class. The second bell rang, which meant class was just about to start.

"Now class, settle down!" Said a familiar voice to Ash and Misty.

Brock, Misty and Ash's neighbour and long time friend came through the door.

"Brock!" Misty and Ash said at the same time.

"I thought you were going to be a doctor or something" Misty teased.

"Umm... well Misty when the opportunity came up for me to teach about pokemon I just had to accept" Brock replied.

"Ha! Sounds to me like a doctor would be a lot better job! And you could find a pretty nurse to be married to forever there" Misty taunted again.

"WOULD YOU JUST SHUT UP!?" Brock yelled, just as he always did when Misty and Ash would tease him about liking every girl that he sees.

"Brock your our teacher?" Ash asked. _But WHY? He thought. Tough Luck I guess... I can tell this class will be hard to pass... there is so many distractions..._

_**So, we figure out Brock is one of Ash's teachers. Will Ash have trouble dealing with arrogant troublemaker Gary Oak? Will Ash have trouble with his old friends he hasn't talked to in a year because he made new friends? Will ash have trouble having Misty and Serena as friends? All of this and more to come soon!**_


	3. Chapter 2: Hunger for Battle!

**Chapter two: (at lunch)**

It was lunch time now, and Ash was sitting at a table with all of his best elementary friends. Misty was to his left, on his right was Drew, and sitting across from him was May.

And then, all of a sudden, Serena stood up from her table and walked over to Ash.

"Hey Ash, is it okay if I sit at your table?" Serena asked

"Of course you can!" May told her. Serena shot a look at her, but then went on to stare at Ash again

"Sure, but I don't know if there is much room at the table. It'll be a squeeze if we all want to fit." Ash answered.

"It's okay, I think we'll be fine!" Serena said as she pulled up a chair and sat down in between Ash and Misty at the table.

"So Drew, and May, how was your summer?" Ash wondered.

"Great!" May replied. "I went to the Kalos region on vacation with my brother Max to see all of the fairy pokemon that live there, and it was awesome!"

"Yeah mine was good too," agreed Drew.

"Hey Ash, did you know that Brock was the cook here too?" Said Misty

"No, I didn't," Ash said still chewing on his sandwich. "But that must be why it tastes so good!" He nearly yelled.

"You're right Ash, the food is really good!" Serena smiled

Soon after, the bell rang, and the next class they would have is battle strategy class, where they would meet a new teacher and would have a challenge waiting for them.

"Why hello class! I am your Battle strategy class and Science teacher, Professor Oak. Some of you may know me, and some of you may have only heard stories, *cough*. Hello Gary, my beloved grandson and Ash, good day to you too."

_Him TOO? Ash thought. Why?_

"Okay class, for your first assignment on the first day of class, you will be assigned a partner, and then you will have to battle them one pokemon on one pokemon. Do not worry about who your partner is, they were pre-picked by the principal here. Now please do not release your pokemon until we get to the outside battlefield." Professor Oak told his class.

Then, he began to read off the names of people's pairings

Gary vs Trip

Ash vs Paul

Misty vs Serena

Dawn vs Drew

May vs Iris

Then, the class began to walk to the battlefield.

"Good luck Ash!" Said Serena "I hope you win!"

"Thanks," Ash whispered back

When they were outside, the class waited. Then after about two minutes of waiting, Professor Oak yelled, "LET THE BATTLES BEGIN!"

"Go, Serperior!" Trip said.

"Serrrr-perior!" The snake-like Pokèmon called out

"Alright Blastoise time to battle!" Gary yelled. He threw the pokeball In the air, and out came a red beam of light, releasing the turtle.

"Blastoise get the first move! Use Hydro Canon!" Gary said. The pokemon quickly followed orders, jumped up and shot a large blast of water from its Canon on its back.

"Serperior dodge it and use dragon tail," Trip replied. The snake burrowed under the ground to dodge, and when it came back to the surface, it's tail was glowing purple.

"Now's your chance Blastoise, use bite on the Dragon tail!" The serperior was easily caught in the blastoises bite attack.

"Serperior, No! Break free!" Trip called, stomping his feet

So, in the first battle, Trip goes down quick and his Serperior is caught in Blastoise's teeth.

"Class, as you see, even though Trip's Serperior had the type advantage, strategy is important, too." Professor Oak said.

"Now, Blastoise, Finish it with skull bash" Gary said arrogantly. Snapping his finger, his pokemon reacted

"Serperior do your best!" Said Trip. He yelled support at his Serperior, but it wasn't much longer.

The skull bash landed a direct hit. And afterword, Serperior was badly hurt and unable to battle. So Gary won his match.

_**As this chapter comes to a close, will ash win his battle? He goes next! What is up between Misty and Serena? Will drama happen on the first day!? What do you think? Please leave a review and let me know what you think! Until then, have a great day, chapter three should come to you tomorrow! Bye!**_


	4. Chapter 3 Battles always lead to drama

**Tough Luck, chapter three**

_**Hey Everyone, it's fanficfanatic500 here, with the next chapter. And yes, I know I promise a new chapter yesterday, but most days I can only handle one chapter, and I did a chapter for a good friend, go check her story out. The authors name Is The Wholocked Pony. Now, it's time for an important chapter. Ash's battle is where we begin. It is aginst his longtime rival, Paul. **_

"Ash, send out your pokemon first" Professor Oak said.

"Okay, Charizard, come on out, I choose you!" The Dragon emerged from the small red and white ball.

"Ursaring, standby for battle!" Paul exclaimed. His bear like pokemon had a ring on its chest, and a tall frame. It was ready for battle.

"Ash, you may begin" Paul told him.

"Okay Charizard, start it off with flamethrower!" The fiery beam landed a direct hit on the Ursaring, hit him square in the chest, and knocked him back some. The ring served it's purpose for Ash's Charizard to have a target.

"Ouch, Urisang took the hit!" Said Serena, wincing at the hit.

"Now Charizard, use dragon tail" Ash said. Just like the battle before, Ash's Charizard's tail began to glow.

"Ursaring, dodge, and use focus blast." Paul commanded casually, just like he was taking a leisurely stroll in the park.

His Ursaring easily moved out of the way, and began charging a yellow ball of energy. Ursaring released its energy, and the move went flying straight for Charizard.

"Wow, it looks like that focus blast landed a direct hit!" Dawn said.

"Yeah it sure did," May answered

"Alright Charizard your fine! Now go! Use slash!" ASH was confident in his pokemons ability.

"Dodge it," Paul said, equally confident.

"Now's your chance Charizard! Flamethrower and wing attack!" It was a dual move, and it hit dead on.

"Ursaring hang in there" Paul Shouted in support.

"Charizard now finish him with slash!"

"Ursaring counter that with hyper beam!"

Both moves were equally powerful, it was a clash of wills.

Both pokemon were down after that. Professor Oak declared:

"On a normal standard, this battle would be a tie. Both pokemon have put up a good fight, and if they continue one may get seriously hurt. But since we are in a tournament here, first pokemon to stand wins."

Both trainers yelled, but Ash's Charizard would emerge victorious.

"Good job Ash!" Serena said, jumping up and down in support.

"Thanks" Ash replied

"My battle is next! See ya! Wish me luck" Serena shouted

"I will, good luck Serena." Ash showed his support.

**(Time lapse)**

It was Misty's Starmie verses Serena's Fennekin. Serena's Fennekin had taken two super-effective water type moves. However, Misty has let her lead get her prideful and her Starmie had taken several scratch attacks.

"Fennekin, finish it with flamethrower!" Serena commanded

"Ha, you think that'll finish me!? Starmie, take this attack and then finish her pokemon with water gun!" Misty taunted.

The flamethrower hit, and Starmie fainted.

"Starmie, no!" Squealed Misty

"Starmie is unable to battle, so Serena wins, despite a type disadvantage." Said Professor Oak.

Then there were the rest of the battles.

Drew beat Dawn and May beat Iris.

The day was over soon. But the drama wasn't quite over for Ash. He and Misty were walking down the long, narrow exit hallway and they would walk home together, just like every other day in elementary school. But Misty however, wanted to speak to Ash alone all day.

"Hey Ash, don't you think that Serena is trying to get in between you and me?" Misty asked curiously.

"No, not really, I just think she wants to be friends."

"Come on Ash Ketchum, don't you see it?"

"No, Misty Waterflower, I don't."

"Well, maybe your so oblivious to the truth, you will never notice. But I take offense to her trying to take you from me."

"Since when was I yours, Misty?" Ash cried out

"You were my friend Ash! I don't want her to take away our friendship!" Misty yelled back

"I can have as Many friends as I want, and still have you as my best friend!" Ash replied

"Well, that's pretty big talk for a 13 year old boy who doesn't even know who his father is, or even care!" Misty finished.

"Misty... that hurt... please take it back so I know you didn't mean it," Ash said in a whisper voice.

"YOU KNOW ASH, MAYBE I DID MEAN IT!" Misty replied.

"Well here is what I think, Misty, I will be close friends with Serena because I don't care what you think!" It was the only comeback ash would have the mental strength to throw at her. He really did care about his friend. They have been best friends since they were in diapers. But the comeback seemed to work.

"If that's how you feel..." Misty ran out the double doors sobbing.

Now Ash felt terrible. When he got home, he was crushed. He began to cry into his pillow on his bed in his room. He had screwed up this time. A great friendship gone. They have had several arguments, but nothing like this. It completely tore them apart. He reached for his phone, but he couldn't gain the strength to. Besides, after what she said, she didn't deserve him, did she?

_**Thanks for reading everyone! Please leave a review or a favorite/follow... I need the support to continue with this story. Don't forget to check out The Wholocked Pony! Thanks to my favorite/follows. I appreciate the support so much, you don't even understand. So here is your suspenseful questions: Will ash and misty make up? What do the winners of the battle get? Who is Ash's father and who is his principal? Will ash find out about dating a girl soon? These and so much more to come not the next chapters! Thanks so much, have a great day! Byeeeeeeeeee! ;D**_


	5. Chapter 4: What have i gotten me into?

_**Hey Everyone, chapter 4 will be a short one, but it fanficfanatic here to tell you to sit back, relax, and enjoy the next chapter, in which Amour Shippers will be happy! **_

"Thanks for driving me here mom" Ash told his mom

"That's fine, have a great day! Don't forget to have Pikachu return to its pokeball!" His mom told him.

"I will!"

"Hey Ash!" Serena called out

"Picachu, return!" Ash said, holding out Picachu's pokeball, and shot a red beam of light to recall it.

"How are you Ash?" Serena asked.

"Good, I'm still kinda hurt from me and Misty's argument yesterday." Ash had talked with Serena last night over the phone about their first day.

"Do you know about what Professor Oak said?" Serena questioned

"No, what was it" He responded

"All of the trainers that won yesterday get to have another match! Isn't that so exiting?"

"Yeah! It sure is! I'm so exited! I can't wait"

"Ash, you are so cute when you get exited about things"

"What is that supposed to mean?"

"Well Ash, that means I like you!" Serena blushed

"Oh... Okay..." _I think this might've been what misty might've been talking about, why was I just so thick-headed and didn't listen to her. She wouldn't have told me that for no reason. She was my best friend. Now I feel even worse. But Serena is a good friend, too. But how do I respond to that? I don't LIKE her, but I wouldn't want to upset her._ Ash thought

"So um... Ash, would you like to go out with me?"

"Yeah, sure Serena, why not?"

"Great ASH!" Serena squealed.

"See ya in class!"

_Great, what have I gotten myself into now?_ Ash thought

_**Thanks for reading everyone! And a shout out to Ninjagogirl4773 for your support in the review you wrote! Again, I appreciate all the support from everyone! I hope you enjoyed and have a good day, next chapter will either be up tonight, or Wednesday! Anyways Byeeeeeeeeee! :)**_


	6. Chapter 5: Roller Coaster Emotions P1

_**Authors Note: Hey everyone, it's fanficfinatic here with chapter 5, more of a filler chapter. This was originally a longer chapter, but I decided to split it up into two chapters. It has been a long time since I updated, but I know we can get back into this story. So sit back, relax, and enjoy this chapter.**_

"Hey Ash, what's wrong?" Serena asks ash after their first class. She waited a bit, Swinging her foot back and forth. "Your worrying me!" She asked again.

"You know, I really wish Misty were here now. I feel bad about what what I said..." Ash bit his tongue, "I'm not really sorry though, she was just being rude to me!"

Serena hugged Ash. She didn't want him to feel like that.

"Even though I'm really not sure if I should apologise or not, I can be concerned about her," Ash said uneasily.

Serena thought he looked pale, and sickly.

"Are you sure you're okay, Ash? I know you two have been friends forever and all of that, but I don't want you to make yourself sick with worry..."

"Thanks for being concerned, but I'll be fine" Ash began walking to his next class after ending the short conversation.

Serena looked at her class list shortly after Ash had gone

**·Math**

**·Pokèmon history**

**·Reading/Writing**

**·Lunch**

**·Pokèmon Training**

**·Battle Strategy**

**·Extra: Cooking, Pokemon Grooming**

Afterword, Serena turned to go to Pokemon history class, her least favorite class of the day. She sighed, but continued walking.

"Hey Ash, what's up?" Called a familiar voice to ash.

"Dawn, hey! I didn't expect you to remember me, after all these years"

Dawn had blue hair, her partner was Piplup, the penguin, and she was Ash's oldfriend from a long time ago. Ash wondered how she even remembered him since they had been friends one year, they had been best buddies through the summer, but when school started, they always were in different classes.

Ash still had one person who always ended up in his class, Misty... Ash stopped the thought quickly. That didn't matter now, she isn't here.

"So Ash, long time no see, how have you been?" Dawn asked

"Well, good I guess, you know, still getting into the routine of things around here." Ash said, holding back how he really felt.

"I know you Ash, I know you well enough to know that something is wrong. Tell me, can't you trust me?" Dawn asked, showing a questioning look on her face.

Yeah, I'm telling you, I'll be fine, I just had an argument with Misty yesterday, and now she isn't here at school... just worried." Ash told her, in a whisper.

"Its all good, Ash. I know you'll be fine. If I could've waited all these years and not hated you, I think one day shouldn't be the end of you're friendship." Dawn said, confident in her statement.

Just then, the bell rang, and Dawn turned around to face the teacher, Brock.  
At lunch, Ash, Serena, May, and Drew decided they would talk after school on an online chat room, and have fun.

Then it was time for pokemon battle classes.

Professor Oak posted the lists of the round 1 winners and their new mashups outside, in the mini battle arena, on the bulletin board.

**Ash vs. Serena**  
**Gary vs. Drew**  
**May: battles winner of Ash and Serena**

"Okay class, watch these battles carefully. Ash, you may release your Pokemon.

"Hawlucha, I choose you!" Ash threw his pokeball In the air, and his hawlucha came out in pose.

"Okay, go Fennekin!" Serena called for Fennekin, threw her pokeball In the air and did a spin.

"Serena, a brave move! You used the same pokemon as you used yesterday!" Professor Oak said. What he didn't know was that is her only Pokèmon.

"Fennekin, show Ashy what you're made of! Use flamethrower!" Serena called. Her fennekin jumped up, and shot a fiery blast at Ash's pokemon.

Ash then said, "Hawlucha, size the hit up, and then use flying press." Hawlucha took the flamethrower to the wing, and jumped up, and did it's classic pose.

"Now fennekin, use scratch." The two moves met and both hit their target.

And then, ash let his thoughts get in the way of the battle, something he has never done before. And soon after thinking about all of his problems, the battle was a blur for him. He remembered hawlucha using high jump kick, missing, and getting hurt. That is when he thought: my pokemon needs me!

"Fennekin, use Ember!" Serena told it, waiting for a result.

Ash had awoken at the wrong time, it was like a dream. He managed to say, "Hang in there," but it wasn't enough.

Hawlucha's eyes became swirls, telling everyone it was to weak to battle.

"Sorry Ash!" Serena said.

"Its okay, Serena, you deserved it. Great job." Ash said. Ash gave her a friendly hug. Ash may have said good job, But he was actually thinking one thing.

_Tough Luck_

**Next chapter: this week**

**Your Questions: Can ash get over his roller coaster emotions? What will happen in the chat room? This and more to come soon!**


	7. Chapter 6: Roller Coaster Emotions P2

Ash was eager to find out about Misty. He was ready to go home to see his mom again, to tell her how his long day drove on and on. Ashy-Boy was exited to log onto everyone's favorite chatting site, an online chat room called Pokèchat, a webpage made for forum discussion for pokemon trainers such as ash (with such an original name, he thought sarcastically.)

On the other side of town, Serena was waiting for Ash to log on to the webpage, so that she could talk to him, and Learn more about him. She was worried about him truly, and she knew how much Ash cared about his friends, especially Misty and his long-term friendship, but she couldn't let Misty Mess up the true love of her life, her dream boy, Ash Ketchum.

**SerenaHeartAsh has logged on.**

May and Drew had been dating for a while, it felt like. Even though it had actually only been about a day, they had been friends forever, as long as May could remember. They did everything together. May thought their friendship was a lot like Ash and Misty's. She knew that she had to do something to help them. So she logged on.

**May10Maple has logged on.**

Drew didn't really have much to say about this whole idea, but Ash is his friend whom he must stand for, and May is his girlfriend, who thinks they need to do this. So he really had no other, _or better for that fact, _idea than to go along with what they were doing.

**I'mDrew has logged on.**

Misty just skipped school today. She really felt sick, and her three sisters just let her stay at home. But Misty did know that she had a chance of talking to her friends on Pokèchat. And sure enough, when she checked, Serena, May, and Drew were on.

**FreeSpiritMisty has logged on**

Ash finally got home.

"Hey sweetie, how was school today?" Ash´s mom asked him.

"Mister Mime!" Mr. Mime, his mom's personal maid and helper pokemon stood by.

" Well..." Ash said, very hesitantly. "It was a really long day, that's for sure. I lost my battle in Professor Oak's class, but Brock's meal was very good at lunch. I guess most importantly mom..."

"What is it Ash?"

"Oh, well Misty didn't come to school today. I am going to find out where she was pretty soon, though." Ash replied, ready to run to his computer any second.

"Okay Ash, just don't go crazy now, okay?" His mom told him

"_Okayyy Mom..." _Ash told her. " I'm not a little kid anymore, you know?" And with that comment, ash ran for his room. He logged on to Pokèchat.

**GottaKechumall has logged on.**

**GottaKechumall: **hey guys, how's it goin?

**May10Maple: **hey Ashy-Boy

**I'mDrew: **Hey dude what's up?

**FreeSpiritMisty: **Hey Ash, aren't you all wondering where I was by now?

**May10Maple: **Yeah, Misty where we're you?

**FreeSpiritMisty: **I was sick, really sick

**SerenaHeartAsh: **Sick, on the second day of school? How unlucky is that!?

**I'mDrew: **It happens...

**May10Maple: **hey, haven't you heard the news?

**GottaKechumall: **May!

**FreeSpiritMisty: **Does it have something to do with Serena's username?

**SerenaHeartAsh: **Yeah! Me and ash are dating! Isn't that exiting!?

Misty knew it. In her room, she nearly burst into tears. It brought back the argument, the anxiety sickness, everything. Her best friend had abandoned her. She knew she couldn't handle what was happening alone.

_**FreeSpiritMisty has logged off.**_

It reminded her of a phrase Ash Ketchum loves to use.

Tough Luck.

**Author's Footnote: Hope you enjoyed, this is a chapter that was supposed to be part of chapter 5, but I decided to split it up into three parts. That would make this part two! So much more to come in the next chapter. The main question: why did Misty log off? My question: Why did I decide to incorporate Social Media Networks into my fanfiction? The next chapter I guarantee by November. I will be doing another chapter for TheWholockedPony, so if you haven't, check her out. Thanks, and if you have comments/questions/ideas post a review or PM me. Enjoy the rest of Your day/night**


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